


My Sister's Boyfriend

by Basketballer3511



Category: Supernatural
Genre: Blow Jobs, Dean Winchester and Sam Winchester in Love, Dean is Jess's Brother, Falling In Love, Fluff, Jessica Moore is the best, M/M, Masturbation, Misunderstandings, Moving In Together, Riding, Smut, Stanford Era (Supernatural), Summer Love, Unrelated Dean Winchester/Sam Winchester, slightly slutty sam
Language: English
Status: Completed
Published: 2021-02-27
Updated: 2021-03-08
Packaged: 2021-03-18 21:00:31
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,625
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29739795
Author URL: https://archiveofourown.org/users/Basketballer3511/pseuds/Basketballer3511
Summary: Jess and Dean are as close as siblings can get. Which is why Dean feels so guilty having feelings for her boyfriend Sam, who has come over to their family's house for the summer.Little does he know that Sam and Jess aren't as close as he thinks they are and Sam is sharing the same feelings that Dean is.
Relationships: Dean Winchester & Sam Winchester, Dean Winchester/Sam Winchester, Jessica Moore & Dean Winchester, Jessica Moore & Sam Winchester, minor Jessica Moore/Sam Winchester - Relationship
Kudos: 42





	1. Chapter 1

**Author's Note:**

> Dean working at his own dealership, Dean and Jess having an awesome bond, and all three of them spending time together and being super happy. Oh and Sam and Dean being absolutely in love. This fic has it all lol. The summertime vibes are strong in this one.

It was his job to rough up the kid that decided that he was good enough to be with Jess. Dean had been protecting his little sister since before he could even remember and even though she was 22 and grown up, she was still the hair sticking everywhere kid sister that Dean loved and shared a birthday with. So he was pretty prepared to say the least, to size up whatever idiot that came arm in arm with Jess for the summer. 

He had his most radiant, I am going to squeeze the ever living fuck out of your hand, but I also am an American sweetheart smile on ready to go when he walked to the door, swinging it wide open just to be attacked by a bear hug from his little sister. 

"Hey, easy on the goods" Dean said into Jess's hair, squeezing his eyes shut momentarily as he enjoyed the feeling of having her back in his arms after a whole semester. 

"I don't see any goods" Jess replied, her smile summertime happy and eyes crinkling as she let go of her brother and stepped back. 

"Just so rude Jessica" Dean joked back, ruffling her hair, as he now, unfortunately prepared himself to see whatever loser with a capital L Jess had brought with her. 

And holy fucking shit that was no loser standing behind Jess. He was taller than both Jess and Dean, which was a feat in itself. He was California tan, a confident, yet also pliable aura around him, and wow Dean was talking about aura's now. Great. 

"Hi, I'm Sam" the kid said reaching forward to shake Dean's hand. Dean was so blinded by the full, dimpled smile that came his way that he had no time to assert his dominance. He instead spluttered out a "I'm Dean" and wow no shit Dean, he probably already knows that, but it didn't matter because Sam was looking at him from under his bangs, a cute, bashful smile on his face. 

And god Dean had to be the worst big brother in the world because he was calling Jess's boyfriend cute in his head and if his heart did not stop thumping as much as it was right now, this was going to be really bad.

* * *

Dinner was a splendid affair... oh wait it wasn't. Their parents hadn't stopped fretting over Jess and Sam, and Dean had to hide his snort into his glass when Jess made a gagging face behind their parents backs.

The only thing better then two miserable siblings, was an equally miserable boyfriend who was sure his neck was going to snap from how much he had been nodding and smiling.

He could tell Jess was zoning this entire dinner out and he could see the same floaty look on her brothers face, causing him to look down and smile. 

He didn't expect much from a summer at Jess's house. He had been told how severely sophisticated her parents were and how... not her brother was. She described basically her twin even though they were four years apart. Thought she did make sure to mention that she apparently had better music taste than him and he was somewhat dorkier then her. How? He was not sure, but he really could not wait to find out. From the three Stark Trek references in the last five minutes alone, that floated over their parents heads, Sam was sure he could feel his heart clambering against his ribcage. 

Jess was pretty sure she was ready to bash her head against one of her moms fancy dinner plates, but she figured that would be non respectable. The glee of returning home was short lived, the only thing making it worth it was Dean and his boisterous laugh causing water to end up in her nose and Sam's giggles filling her ears. 

The three practically ran into the kitchen once dinner was over. They were no longer stifling their laughs, leaning into one another as Dean showed them the burgers he had stowed away in a secret hiding spot just for after dinner. 

"If I eat another piece of rabbit food, I am going to seriously consider going into witness protection" Dean said around a large bite of burger and french fries. Jess snorted, eating her burger in a slightly less aggressive way than her brother. 

"Salad won't kill you, high cholesterol probably will though" Sam surprisingly pitched in. He had been fairly quiet, laughing along with the siblings jokes. Dean raised a brow in surprise and his lips quirked into a large smile when he heard Sam speak. 

"College boy has jokes" Dean said, giving a proud smile to Jess, who smiled fondly at both of them. 

Sam smiled sheepishly, choking slightly on his soda. 

"When are you heading to work tomorrow?" Jess asked Dean, helpfully diverting the attention off of Sam. 

"Around 9" Dean said, throwing a french fry at her, which she threw right back. 

Jess had proudly told Sam before about how Dean owned and work on antique cars at his own dealership and Sam figured this was the best way for him to get to know Jess's older brother. 

"I barely know a thing about cars, I would love to come to work with you" Sam said, batting sincere eyes and furrowed brows in full force to Dean. He knew it wasn't really playing fair, but a whole day with Dean? He could afford to pull all the stops he needed to.

The kid was a literal puppy with fluffy hair to boot. Long legs and dimpled smile and Dean really had no chance, what with the breathless voice the kid used and the most sincere eyes. Hopeless was how Dean felt and Jess was sitting right here, smiling at the two of them. 

"Uh, yeah. Sure" Dean quickly replied, looking at Jess for reassurance. This was an epically bad thing. A whole day with Sam, yeah no, but Jess and Sam were both looking so elated that Dean couldn't say no even if there was a gun to his head. 

* * *

Dean fretted with his collar, staring himself down in the mirror. "You're not going to flirt with Jess's boyfriend" he whispered to his reflection, pointing sternly at himself. 

As soon as dinner was over and Jess and Sam had went into their own room, Dean was alone with himself and thoughts of Sam. The guilt consumed him as flickering images of Sam on top of him, his pretty mouth open as Dean licked into it, while grinding into the kid. Dean tried. He can't say he didn't try to avoid thinking of Sam while getting off, but at the last moments when he was just about to be tipped over to the edge, the sweet images of Sam's grin filled his mind and he was off. Spilling all over his hand and letting out a self deprecating groan when it was over. 

God he was fucked was the last thing he said to himself last night and the last thing he said to his reflection now, before turning away quickly and making his way downstairs. 

Sam was waiting for him at the foot of the stairs, a blinding grin and floppy hair, accompanied with a slightly baggy suit adoring his long limbs. 

"Morning" Sam greeted, dimples in full force and Dean was going to choke on his spit. "Yeah, yes. Morning" Dean replied, nodding firmly and oh god that hurt his neck. 

"Do I look alright?" Sam asked, head tilted down, giving a shy look to Dean. 

Dean was going to die right here and now. "Yeah, you should be good" Dean replied, rubbing his neck biting his lip to not accidentally spill his true thoughts of "yeah Sam, you look absolutely great. Hey would you be cool if I fell down to my knees and blowed you right here, right now?" 

Sam nodded, bright smile returning. "Thanks, you look really good" he told Dean, and was that a flirty smile Sam was using? No way. No freaking way Dean get your head out of the gutter. 

Dean did choke on his spit this time, coughing and spilling out a choked out "thanks." Sam smiled sheepishly at Dean, thumping him on his back before following Dean out of the house for a day of work. 

Sam had pulled out the full smile, the shy, breathless voice he knew usually worked on people to get what he wanted on Dean and it seemed to kind of, sort of work. 

Dean looked like he was going to rip his tie out throughout the ride and kept glancing over at Sam, before roughly turning his head whenever Sam returned his gaze so that was a plus. 

He couldn't stop the smile on his face as Dean went on about cars, showing him models and parts. 

"You know a lot more about cars than you let on last night, Sammy" Dean said once lunch came around, the two's knees knocking against one another as they sat. 

"Sammy?" Sam teased, eyes fluttering up to Dean's face. "Sorry I always give nicknames to people" Dean replied, ready to continue his apology, but Sam stopped him before he could apologize anymore. 

"I like it, except don't let Jess know. She'll tease me forever" Sam said with a grin to Dean, as if the two were in on some private joke. Dean nodded, tensing up at the mention of Jess. God Jess, I am so sorry Dean thought. He was going to buy her a bunch of plants for her room this weekend. It was the least he could do for having a stupid crush on her boyfriend and now spilling out a nickname that only he could call Sam. Fucking great. 

"I, uh, just wanted an excuse to hang out with you" Sam admitted after a couple moments of them just eating. 

Dean looked up at Sam, feeling himself flush a little under that intense stare that Sam did. "Right, getting to know your girlfriends brother" Dean replied, forcing a grin. 

Sam frowned and tilted his head to the side, "what? No" but he was cut off by someone calling for Dean. 

The rest of the day was mainly just Sam sitting around and smiling whenever Dean passed by him. Giving Sam plenty of time to ogle Dean in his suit and appreciate how well Dean worked with people. 

Sam wasn't even aware this was a fantasy he had of guys in suits, but with rain starting to fall steady outside and a hand sneaking its way down his front, Sam was aware that anything would do as long as it had Dean's face involved and the thought of his thick, calloused fingers tracing across his skin. 

The suit clung just perfectly on Dean and Sam was caught between wanting to crowd the shorter man against any car or having Dean hitch one of his legs up and have his way with Sam. 

Sam wasn't this slutty even in his own thoughts, but god Dean made his mind and dick go rogue. He spread his legs and hitched himself down the bed a bit more, biting back a moan once his hand finally wrapped around his dick. Slick pre-come gathering at the crown, which he slid down his length. With a handful of his cock and his balls rolling between his other hand, Sam was pretty sure he was ten seconds away from coming with thoughts of Jess's brother running his hands all over him. 

He reached down a little further, sucking on his finger before bringing it back down and rubbing his hole in circular motions that had him gasping out into the open room. He prodded his finger gently into himself, the tightness and slight stretch and burn had him clinging onto his fingers and riding them into the mattress. He could imagine Dean teasing Sam into oblivion, one finger, then another, and another, and god he was coming into his hand and clenching onto his finger.

If he wasn't so high and boneless from his orgasm he'd be a little embarrassed by how quickly he had come, but he honestly couldn't care less. 

* * *

Sam groaned into the pillow, mumbling "5 more minutes" when Jess forcefully pushed at his arm. 

"Wake up sleepyhead" Jess said with a laugh, sitting on his back. Sam just groaned louder reaching behind him to tickle her, and was met with more of Jess's giggles. Sam laughed into the pillow, rolling so that he was able to face her. 

"Do we have to go to the party tonight?" he asked, using his puppy dog eyes. "Those do not work on me Samuel" Jess said, shoving on his chest. 

"Yes, but Dean already promised me that had an in with the chef so we can gorge ourselves, while my parents entertain their friends." 

Sam nodded, "I guess I can work with that." Catching Jess off guard he pushed her off and crowded on top of her mercilessly tickling her. "Sam!" she yelled, clutching her sides and laughing so hard only breaths of air were coming out. 

Dean passed by Jess's door, toweling at his wet hair when he heard a groan from her room and Jess's laughs. Dean sped up, grimacing. So Sammy liked morning sex, great. Another useless fact for Dean to fret over and want to be thrown to the wolves. 

This was torture. Pure torture. Why couldn't Jess just date an ugly dork, not a hot, tall, built like a god dork? 

* * *

There were fairy lights strung up in the backyard, cocktail dresses, and fancy, fruity drinks that Dean had been sipping from since the first guests began to roll in. 

"Dean, how many "Malibu Sunsets" can you drink" Jess asked, poking him with her elbow. "A billion" Dean replied, grin bright and sloppy, and oh yeah he needed to slow down. 

"I really will never get over how much you like girly drinks" Jess said in disbelief. "Hey they are not girly" Dean defended. "The drink is called Malibu Sunset and something that Carrie Bradshaw would probably drink" Jess replied. Dean mumbled in defeat, "they're really good" Dean jokingly whined, making Jess laugh and wrap an arm around him. 

Dean held onto her, enjoying the floating feeling he felt from the drinks, the buzz of people talking, and music playing all in the background as he and Jess stayed away from the crowd in their own space. 

"How do you like Sam?" Jess asked, her eyes bright and twinkling, and so unsuspecting of how awful of a big brother Dean was. 

Dean didn't know if he felt better or worse when he head their mom call for Jess. Jess groaned into his neck, before unwrapping herself from Dean, and grabbing onto his hand and forcing him to where the party was. 

Their parents made Jess and Sam stand in the gazebo, while their mom thanked all the guest for coming. 

"Now, we are so happy to see Jess here with Sam. They are a gorgeous couple and we couldn't be happier" their dad said. Someone yelled "kiss!" from the crowd and Dean was going to find them and put pepper in their cake. 

The guest and their parents looked expectantly at Jess and Sam, who both looked like deers caught in headlights. Sam and Jess whispering protests to their mom who was politely nodding and whispering from the corner of her mouth. 

Whatever their mom said made Sam and Jess stop their fussing. Both looked at one another, grimacing as they leaned into the kiss. 

Personally they looked like they had fallen asleep in the middle of their kiss, but that was probably Dean's jealousy impacting the logical part of his brain. He was supposed to be happy goddamn it. Jess found herself a nice boy, who wore khakis when asked to and who wore his hair kinda long, but with the sweet face created from Michelangelo himself probably it was hard to see any negatives in Sam. Poor kid was embarrassed to kiss his own girlfriend, couldn't get more good than that. 

Anyway Sam and Jess were happy and Dean was happy because they were good people. Dean turned away after a second, he really couldn't stomach this right now. Maybe in a week or two when everything settled within Dean and he could pretend to hang out with Jess's boyfriend with no issues, but right now he did not need to see this kiss and probably more public displays of affection from happening. 

"That felt like kissing my sister, if I had one" Sam complained, wiping his lips exaggeratedly. 

"So if you kissed Dean would it feel like kissing your brother or...." Jess joked with a devilish grin. 

"Shut it" Sam grumbled, pushing lightly at her arm. Jess sat down at the table with a huff, "I will never ever kiss you again. I mean Sam you bit my lip!" 

Sam groaned, "I got nervous because we were in front of all your parents friends and you yanked my hair!"

Jess rolled her eyes, "you're 8 feet tall, I couldn't just get a step stool, so I had to get creative." 

"By giving me premature balding?" 

Jess punched his arm lightly, looking at whoever was coming to their table. 

"Who are you looking at?" Sam asked, before he was greeted to the site of Dean. 

"Hey lovebirds!" Dean greeted, putting on his best overly happily customer service voice on. 

"Do not call us that" Jess said, glaring at Dean. 

Dean frowned at her, "why not, that was quite a kiss" he said wiggling his brows. 

"We aren't even dating. Mom and dad just assumed and can't accept that I'm not going to get married as soon as I get out of college."

Dean felt like a choir was singing "hallelujah" behind him and fireworks were going to go off soon. Jess and Sam were not a couple. Sam may have actually be flirting with Dean. Dean could possibly have a chance with Sam. Sam. Sam. Sam. His brain repeated in glee. 

"Wow" Dean said, grinning as he took a sip of his beer. "I am shocked, we all thought that you two were you know.."

Jess sighed, "I would have told you Dean if I was dating someone. I just told you Sam was coming."

"Yeah that's right" Dean said, shaking his head at his own lapse of judgment. 

"Also I'm pretty sure Sam is not that into me" Jess said with a grin to Sam. Sam sputtered, looking between Dean and Jess. 

Dean's brain clicked fully online, his grin wide as he looked at Sam. "Oh, does Sammy have a crush on someone?" Dean teased, getting a glare and pink cheeks from Sam. 

"Sammy does" Jess said in sing-song voice, ducking away from the cake pieces Sam threatened to throw at her. 

Dean waited for Jess to go before sliding into the chair she had previously occupied. "So you come here often" Dean said, with a flirty tone and his trademark smirk, as he placed his arm behind Sam's chair, lightly rubbing his thumb over Sam's suit covered back. 

"Does that ever actually work for you?" Sam asked with a snort, leaning closer so he and Dean were face to face. 

"Almost never" Dean replied, grinning his real smile to Sam. "That's what I thought" Sam said, licking his lips and raising a brow to Dean. "You know I'm usually not this easy" Sam said, continuing their cheesy dialogue. "Glad I bring that out in you" Dean said, so close that Sam could feel his smile against his lips. Sam leaned in and closed the distance, finally feeling Dean's lips on his. 

Dean cupped the back of Sam's neck, running his hands though Sam's hair and letting the slow, soft feeling of Sam's lips guide the kiss. The kid was soon licking into his mouth, practically on his lap, before pulling back. Hair slightly sticking up and cheeks and lips pink. Sam surged right back, smiling into the kiss as he felt Dean groan in relief. 

"We should probably head inside before we give everyone a free show" Dean said, resting his forehead on Sam's. Sam kissed Dean's nose, before nodding. Yanking Dean up; the two stumbling and laughing as they made their way to Dean's room. 

Sam lowered himself on Dean's cock, grinding down, before lifting up a bit again. Repeating the process over and over, until Dean could only hold onto Sam's hips and look up at him like he had discovered a new element. 

Sam moaned appreciatively when Dean's cock dragged against his prostate, breathless with need and exertion. 

Dean looked at Sam's red face and glazed eyes, shifting himself a little on the bed so he was sitting up more. 

"Want me to take over?" Dean asked, kissing Sam's chin. Sam nodded, falling forward and resting his head on Dean's shoulder and nuzzling his nose and lips over Dean's overheated skin. 

Dean held onto Sam's hips, thrusting lightly, before moving so that now Sam was on his back and Dean was able to mount him better. 

Sam let out a loud moan, legs spreading wider and one thrown over Dean's shoulder. Dean devoured Sam's mouth, feeling Sam clench onto him and feeling how soaked he was from lube and spit. 

Sam held onto Dean's arms and back, neck tipped back in pleasure and eyes squeezed shut. Dean pressed kisses all over Sam, tucking him close even after both finished. 

Sam woke up to kisses pressed on his shoulder and his skin being licked from Dean's teasing tongue. Dean had woken up to Sam clinging onto him and burning him with all his heat. The bed smelt like Sam, sweat, and sex and Dean was breathless in his want for Sam. 

He kissed Sam's skin gently, rubbing his cheek against the warm, tan skin, before he felt Sam start to shift and become more alert. 

"Morning" Sam said, lifting his head up to grin at Dean, before dropping it back down to rest on Dean's chest. 

"Morning" Dean replied, curling his hand though Sam's hair and playing with it. 

"So how do you think your parents will feel about me being with you?" Sam asked, feeling Dean wrap his arms around his waist as he looked into the mirror. Towels hung low and water droplets drifting down their skin. 

"Well considering they thought you were with Jess just last night, we may want to take it slow" Dean said with a snort, kissing Sam's shoulder blade. 

* * *

The two really didn't have to worry much about telling Dean's parents that it was actually him who Sam was with, because when they went down Jess had a bright smirk and looked like she was barely concealing her laughs and their parents looked disapprovingly at Dean. 

Sam gave a wide eyed look to Dean, who looked at him equally frightened. 

"You boys were quite loud last night" Jess said in a falsely parental voice. 

"Just keep it down next time" their parents said with a grimace. 

"I'm so sorry" Sam said, giving them an apologetic version of his puppy dog eyes that made even Dean want to apologize. But he would not, because he was a sex machine who did not get embarrassed. Okay fine, his heart was beating wildly and he probably won't be able to look into his parents eyes for a week, but that was between him and his brain. 

Sam's skin darkened with each day he spent with Dean and Jess. The three were inseparable, bike rides, hikes, swimming all day. Jess's hair lightening, Sam's hair growing longer, and Dean's freckles darkening defining their time together. 

The town and their home was filled with laughter, running footsteps, and the smell of ice cream, pie, and burgers. 

Sam lay on his back in the pool, perfect view of Dean sitting on the lawn chair, legs spread giving Sam quite the view. 

"Stop ogling my brother" Jess said in Sam's ear, causing him to jump in fright and get water in his eyes. 

"Jess!" Sam complained, racing after her. 

Sam clung onto Dean, shirt sticking to him and Dean reaching up to swipe at Sam's bangs so the sweat didn't fall into his eyes. 

The two had been in the sun for hours, alternating between laying on their backs, stomachs, and on top of one another. Now it was dark, the two tired out and Sam feeling like he needed Dean all over him as they walked back home. 

Sam laughed contentedly during their nightly family dinner, tongue tracing his lips before he took a sip of his beer, turning his head to see Dean staring at him with a wide eyed smile. 

Dean pressed a kiss onto Sam's red cheek, making sure Sam was full and rehydrated. 

Time with Sam was slow, while also dizzying in its speed. Sam was up to try anything as long as it was reasonable, slightly less wild than Jess, but equally joyful as he held onto Dean daily and crowded into one another till no one could tell what was Sam and what was Dean. 

Dean woke each morning to Sam. Tan skin, long limbs, and sometimes hair in his mouth, but he was happier than he had ever been. Long nights spent talking, singing at the top of their lungs, or just laying in the comfort of one another. He was happy and Sam was too. 

* * *

"So you'll text and email me right and come visit?" Sam asked, holding onto Dean's hand and looking down at their conjoined hands. 

"Course Sammy. Plus I have to visit Jess and you two do share an apartment so it would be kinda hard to avoid you" Dean joked. 

"Jerk" Sam grumbled, letting Dean pull him into a hug. 

"Bitch" Dean replied, kissing the top of Sam's head and holding him close. 

"Oh summer love" Jess said, breaking their moment and sliding next to Dean. 

"Not just summer love" Dean said, grinning at Sam, who ducked his head down in an attempt to hide his blush, smile, and slightly wet eyes. 

"Bye kiddo, good luck this semester. I'll see you in about a month" Dean said, hugging Jess tight. 

He waved his little sister and his boyfriend goodbye, giving them obnoxious air kisses as they drove away, Sam looking out the window and waving until he could no longer see Dean. 

* * *

Dean ran his hands through his hair, feeling slightly nervous as he walked up to Sam and Jess's apartment. Sure him and Sam had been texting, talking, and emailing as much as possible, but what if Sam just wanted to be friends? 

All thoughts of Sam possibly finding someone better was cut off when two pairs of arms wrapped Dean in a bone crushing hug. 

"Can't breathe guys" Dean said, hugging back. 

Jess pulled back first, smiling a shit eating grin at Dean. Sam held on longer, tucking himself into Dean and kissing Dean's neck, jaw, and then mouth. 

"God I missed you" Sam said against Dean's lips, laughing when their noses rammed together. 

"You just missed my body" Dean teased, blushing at Sam's worse, because yeah he had missed Sam more than anything and the fact that Sam returned those feelings was too much for him. 

"Yeah that's it" Sam said, kissing Dean again and tightening his arms around Dean even more. Dean was pretty sure having his arms full of Sammy was all he ever could want in life. "I really missed you too, you know" Dean said resting his forehead on Sam's and cradling Sam's face in his hands. 

"I know" Sam replied, lips pressed firmly onto Dean's feeling like he needed to consume Dean and be consumed by him in turn. 

"You should see how many more plants we have now" Sam said once they finally pulled away and were sure they would survive without having lips and hands all over each other, even though Dean still left his hand on the small of Sam's back and Sam kept glancing back as if he didn't believe Dean was here. 

"God Jess and her houseplants" Dean groaned. 

"Hey!" Jess called out. 

Sam smiled and laughed with the two siblings. Positive that his cheeks were going to hurt from smiling so much and his throat would burn from all the laughter and stories they were going to tell, but Sam really couldn't ask for anything more. 

Dean kept looking over at Sam, smiling wide and looking at Sam like he was the only one to exist and Sam hoped that Dean knew that he was it for Sam forever as well, but he figured he'd ease into that when they weren't all eating pie and stealing fries from one another. 

He was happy here. With Jess's laugh loud in his ears and Sam's dimples under his fingertips, Dean knew this was it for him. 

Jess couldn't stop her laughs from leaving her mouth, having Dean here to brighten their apartment. Making it feel more like a home all three of them. 

They were all happy. Home with one another. 


	2. Moving Home

**Summary for the Chapter:**

> Dean has a big surprise to tell Sam and Jess
> 
> Warnings: Smut

Dean was sure every inch of his soul was being sucked out of him. I mean that floppy haired kid had a mouth on him that made Dean want to raise his arms up to the sky and sing in a gospel. 

Sam was all grins, kissing Dean's hipbone with his split soaked lips. Pink and opened mouth returned licking and sucking, hallowing his cheeks as he moaned around Dean's cock. Fighting to keep his eyes open so he could look through blurry eyes at Dean's face as he fell apart. 

He licked Dean's balls, kissing and sucking, before running his tongue on the underside of Dean's cock. 

Dean had never heard himself make the sounds he made then when he and Sam got together. He felt himself coming, Sam licking, sucking, and moving his hands up and down his cock all to make Dean feel that he was going to pass out. 

Dead from the hands and mouth of Sam Winchester. Not a bad way to go. 

"Sammy" Dean finally rasped out when his brain returned online and he no longer felt like he had ran a race against an Olympic track runner.

"You still talking?" Sam asked, crooked smile as he rested his head on Dean's stomach. 

"Shut it" Dean said, pulling at Sam's hair before making him come up. Sam bracketed his arms around Dean, ducking his head down to kiss Dean's bitten lips. 

"I swear when I can get my arms to move again I am going to fuck you into the mattress." 

"Me and my cheap college mattress are waiting on it" Sam said, leaning into the kiss that Dean gave him. 

Dean had not been planning on spending two days just in Sam's bed. Sweat soaked sheets, Jess knocking on the walls and yelling at them anytime they got to loud. Dean was drowning in Sam. Being able to hold Sam against his chest, press kisses on his forehead whenever he pleased. 

"Before I came here, I started looking for some jobs around here. Maybe be closer to you and Jess" Dean said, nervously looking at Sam. 

Sam lifted his head, shuffling to lean on top of Dean. "You're going to move out here?" not even bothering to hide the enthusiasm and pure fucking joy that Dean and him wouldn't have to talk on the phone until they fell asleep anymore. They wouldn't have to go over their texting limits because they would constantly be updating one another thought text if they couldn't talk on the phone. No more blurry photos, now Dean was real next to him. In his bed. In his arms. In his--okay his and Jess's apartment. 

"Yeah if you guys are okay with that--" Dean was cut off from continuing before Sam was throwing his entire body on top of Dean's. Kissing Dean all over and smiling so wide that Dean knew this was one hundred percent the best decision he had ever made. 

"God, I can't even believe this Dean" Sam said, cradling Dean's head, "Jess is going to be so excited." 

Before Dean made his big announcement, Dean made sure to fulfill his promise. 

Sweat dripped down from his hair onto Sam's chest, but Dean couldn't really care. Grinding into Sam and making sure his dick was felt all the way inside, until Sam could only let out breathy moans and grip onto Dean's arms. 

It didn't matter how many times Sam had Dean inside of him, he still felt stuffed full by Dean's cock. Felt himself go crazy as he was rocked into the mattress and reduced to just saying Dean's name over and over. 

To be fair it wasn't just Sam losing his mind, Dean too held Sam close to him. His only thoughts being Sam and making sure Sam felt as good as possible. 

Once they were finished, panting into each other's mouths and stealing not so last moments of pleasure, Sam and Dean lay boneless in bed. Cuddled close in bed, hands held, and fingers running down one another's bodies. 

\----

When Jess entered the apartment and heard the news that Dean was going to be moving to Stanford with them, she jumped into Dean's arms. Squeezing him and grabbing at Sam to pull him into the group hug. Sam laughing in one ear and Jess in the other. 

"Oh god I think you both burst my ear drums" Dean rubbed at his ears. 

"Shut up!" Jess and Sam said simultaneously, squeezing Dean harder.

**Notes for the Chapter:**

> I wanted to add another chapter because I had this idea that Dean would join Sam and Jess, and wanted to elaborate on it.
> 
> Comments and kudos are appreciated!

**Author's Note:**

> I really loved writing this. I hope I did Jess's character justice and that you all enjoy this!


End file.
